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Outfitting adventure since 1935, our boat shoes are tried-and-true icons of seaworthy style. True to our heritage they’re still hand-sewn using time-honored craftsmanship, with premium materials and the wet/dry traction that made them legendary. Here we’ve given our boat shoe a style spin with a touch of sneaker styling while upping the ante on wearability with a cup sole and even more cushioning. Classic, may we introduce cool and comfortable?

Jeff1987Amazing lookThis show is perfect for the office or a night out. I love how it is a great balance between a sneaker and dress shoe! Colors are great as well and have received lots of compliments. Plan on buying all colors of the sperry cup.

Amazing look

Mar 04, 2019

This show is perfect for the office or a night out. I love how it is a great balance between a sneaker and dress shoe! Colors are great as well and have received lots of compliments. Plan on buying all colors of the sperry cup.

JSGreat pair Sperry has done a great job with this one!I’ve always owned a pair of Sperry boat shoes however over time the sole just gets worn out and no longer support my foot. When I saw these I said “bingo those are gonna last” after owning this pair for a while I have to say Sperry has hit a home run with this one!

Great pair Sperry has done a great job with this one!

Feb 27, 2019

I’ve always owned a pair of Sperry boat shoes however over time the sole just gets worn out and no longer support my foot. When I saw these I said “bingo those are gonna last” after owning this pair for a while I have to say Sperry has hit a home run with this one!

ChrisEStyle Plus ComfortHaving worn Sperry boat shoes for many years, I was thrilled to see this Sperry Cup boat shoe with a sneaker bottom. My “senior” feet are enjoying the comfort, but the style is classic Sperry boat show. Win win.

Style Plus Comfort

Feb 26, 2019

Having worn Sperry boat shoes for many years, I was thrilled to see this Sperry Cup boat shoe with a sneaker bottom. My “senior” feet are enjoying the comfort, but the style is classic Sperry boat show. Win win.

20% OFF SITEWIDE: Take 20% off your purchase at OnlineShoes.com through 4/1/19 at 11:59pm EST, or while supplies last. To redeem, use code THINKSPRING at checkout. Offer applies only to orders on OnlineShoes.com. Some restrictions may apply. Not valid on prior purchases, excluded merchandise, clearance gallery items, gift cards or e-cards, or purchases from retail stores or other websites. Cannot be combined with any other offer.